Acyclic chlorohydrocarbon can be prepared by reacting corresponding alcohols with hydrogen chloride (“Traité de Chimie organique” by Grignard and Baud, (Paris 1935, Volume III, page 249). This reaction can be carried out using a catalyst, such as Lewis acids. In addition to Lewis acids, examples of suitable catalysts include iron chloride, aluminum chloride, arsenic chloride, antimony chloride, tin chloride, and zinc chloride. Other suitable catalysts include amine hydrohalides, in particular amine hydrobromides and amine hydrochlorides. For example, such catalysts include primary, secondary, or tertiary amines with unbranched or branched, acyclic or cyclic carbon chains, or amines having aromatic groups. In particular, they may also be heteroaromatic amines, for example, alkylpyridines. EP 0 789 013, DE 101 58 376, and DE 102 47 497 describe a continuous process for preparing alkyl chlorides by reacting alcohols with hydrogen chloride in the presence of a catalyst, for example, an aqueous alkylpyridine hydrochloride solution.
The Derwent Abstract for JP 53-015303 describes the preparation of alkyl halides by reacting alcohols that have at least 4 carbon atoms with an aqueous solution of hydrogen halide in the presence of quaternary ammonium compounds as a catalyst. JP 53-015303 describes a method for the preparation of stearylpyridinium bromide catalyst, which involves stirring together a mixture of 1 mol of stearyl bromide and 1 mol of pyridine at a temperature range from 80° C. to 100° C. for 5 hours. To prepare lauryl chloride, a mixture of lauryl alcohol and concentrated hydrochloric acid can be heated at an elevated temperature for 24 hours. In Synthesis 11 (1988), 868-871, Jursic describes the reaction of primary alcohols with aqueous hydrochloric acid in the presence of micelles (as phase mediators), such as hexadecyltrimethylammonium bromide and hexadecylpyridinium bromide (cetylpyridinium bromide). The alkyl chlorides produced by such method can be isolated by following a complicated extraction step with petroleum ether, a filtration through silica gel, and a subsequent distillation under reduced pressure. For example, octyl chloride can be obtained with a purity of 96%.